Synthesis of new brassinosteroid 24-norcholane type analogs conjugated in C-3 with benzoate groups

0545889 - ÚEB 2022 RIV CH eng J - Journal Article
Ferrer, Karoll - Díaz, K. - Kvasnica, Miroslav - Olea, A. F. - Cuellar, M. - Espinoza, L.
Synthesis of new brassinosteroid 24-norcholane type analogs conjugated in C-3 with benzoate groups.
Molecules. Roč. 26, č. 4 (2021), č. článku 1173. E-ISSN 1420-3049
R&D Projects: GA MŠMT(CZ) EF16_019/0000827
Institutional support: RVO:61389030
Keywords : 24-norcholane * Analogs * Benzoate esters * Brassinosteroids * Conjugated in C-3 * Rice Lamina Inclination Test * Synthesis
OECD category: Biochemistry and molecular biology
Impact factor: 4.927, year: 2021
Method of publishing: Open access
http://doi.org/10.3390/molecules26041173

The metabolism of brassinosteroid leads to structural modifications in the ring skeleton or the side alkyl chain. The esterification and glycosylation at C-3 are the most common metabolic pathways, and it has been suggested that conjugate brassinosteroids are less active or inactive. In this way, plants regulate the content of active brassinosteroids. In this work, the synthesis of brassinosteroid 24-norcholane type analogs conjugated at C-3 with benzoate groups, carrying electron donor and electron attractant substituents on the aromatic ring, is described. Additionally, their growth-promoting activities were evaluated using the Rice Lamina Inclination Test (RLIT) and compared with that exhibited by brassinolide (used as positive control) and non-conjugated analogs. The results indicate that at the lowest tested concentrations (10-8–10-7 M), all analogs conjugated at C-3 exhibit similar or higher activities than brassinolide, and the diasteroisomers with S configuration at C-22 are the more active ones. Increasing concentration (10-6 M) reduces the biological activities of analogs as compared to brassinolide.
Permanent Link: http://hdl.handle.net/11104/0322515